When Remote Gets… Awkward

Remote-first life can be amazing, but if you’ve lived it, you know it comes with a quiet kind of awkwardness.

You’re in meetings with people you’ve never actually met. You reread messages to avoid sounding too blunt or fake. You hesitate to joke or reach out, unsure how it will be received. You don’t know what bothers someone, or what makes them laugh.

And then there’s Zoom. The awkward silences. The small talk you feel obligated to make. The energy that doesn’t quite translate. We’ve all been there, trying to connect, trying to be warm, but always a little out of sync.

So we decided to change that. Not with better tools or tighter processes, but with something way simpler:

A trip. To Brazil. Together.

The Journey Begins: Coming Together in Brazil

So, what happens when you fly 26 teammates from eight countries into Brazil for five days of fun, food, and friendship?

You get the kind of week you’ll always remember, and a reminder that the best kind of team-building doesn’t involve work at all.

For a whole week, our remote-first team met up in São Paulo for our first full-company retreat. We had developers, designers, project managers, quality assurance engineers, and leadership joining from Spain, the U.S., Mexico, El Salvador, Nicaragua, Argentina, Brazil, and Italy. Some of us had worked together for years without ever meeting in person… until now.

The goal? To connect IRL and deepen the bonds that make remote work actually work. We leaned into Brazil as a theme: good vibes, good food, good drinks, and good fun. And São Paulo delivered.

A Week of Joyful Chaos

Our days were packed, with just the right mix of relaxing mornings and late-night dancing. From 10 a.m. to 10 p.m., the week was filled with fun activities and ridiculous amounts of laughter. Some highlights:

• A mindfulness session to start the week with intention
• Go-kart racing and board games for friendly competition
• Cooking classes, karaoke, and graffiti workshops to bring out unexpected talents
• Analog photo contest with disposable cameras, where the whole team voted for the best snapshot of the week
• And of course, Brazilian food and drinks every chance we got

By midweek, the jokes were flowing like caipirinhas. Quiet teammates turned out to be secretly hilarious. People looked nothing like we imagined; way taller, way shorter, and in one case, an undiscovered breakdance pro.

From Coworkers to Friends

What made this retreat unforgettable wasn’t just the activities, it was the people. The warmth. The shared feeling that we’d landed in something special.

One of our event planners captured it perfectly: “You got it good.”

And we do.

Emotional speeches, spontaneous dance-offs, and the kind of late-night chats you remember for years; it all added up to something surreal, yet grounding. We came back home not just more aligned, but more connected.

The Real Outcome

Looking back, the retreat gave us more than just great memories, it gave us answers to challenges we didn’t even realize were weighing us down. After spending a week together, we’re no longer guessing how to connect. We know each other. We know who prefers voice messages and who loves a good meme. We know who needs time to think and who’s going to bring the jokes. The awkward silences? Gone. Communication just flows now, more human, more honest, more us.

Inside jokes, shared memories, silly photos, custom Slack emojis, they all became little shortcuts to trust. And that trust shows up in our work. Collaboration is smoother. Meetings are easier. Feedback feels more natural. Productivity didn’t go up because we work harder, it went up because now, we’re truly working together.

So, How Do You Build a Team?

You unplug. You play. You show up as your real self.

That’s how you do it. That’s how we did it.

Now, let’s get back to building cool things. 👊🏻